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【结 构 式】

【分子编号】55525

【品名】tert-butyl 6-chloro-9-[(1R,4S)-4-({[(2-nitrophenyl)sulfonyl]amino}carbonyl)-2-cyclopenten-1-yl]-9H-purin-2-yl(formyl)carbamate

【CA登记号】

【 分 子 式 】C23H22ClN7O8S

【 分 子 量 】591.98876

【元素组成】C 46.67% H 3.75% Cl 5.99% N 16.56% O 21.62% S 5.42%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

The reaction of 2-azabicyclo[2,2,1]-5-hepten-3-one (I) with 2-nitrophenylsulfonyl chloride (II) by means of BuLi in THF gives the sulfonamide (III), which is condensed with the chloropurine (IV) by means of Pd[P(OPr)3]4 in THF or NMP to yield the adduct (V). The N-protection of the formamide group of (V) with Boc2O and NaH in THF affords compound (VI), which is reduced and deprotected with NaBH4 in methanol to provide the N-Boc protected chloropurine (VII). Finally, this compound is treated with hot HOAc to furnish the target chloropurine (VIII) (see schemes 14673102a intermediate (VIII), 14673103a intermediate (VIII), 14673104a intermediate (IX), 14673107a intermediate (XII), 14673111a intermediate (IX) and 14673113a intermediate (XIII)).

1 katagiri, N.; et al.; Efficient synthesis of carbovir and its congener via pi-allylpalladium complex formation by ring strain-assisted C-N bond cleavage. J Org Chem 1997, 62, 6, 1580.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 55527 2-azabicyclo[2.2.1]hept-5-en-3-one C6H7NO 详情 详情
(II) 32624 2-Nitrobenzenesulfonyl chloride 1694-92-4 C6H4ClNO4S 详情 详情
(III) 55522 2-[(2-nitrophenyl)sulfonyl]-2-azabicyclo[2.2.1]hept-5-en-3-one C12H10N2O5S 详情 详情
(IV) 55523 6-chloro-9H-purin-2-ylformamide C6H4ClN5O 详情 详情
(V) 55524 N-({(1S,4R)-4-[6-chloro-2-(formylamino)-9H-purin-9-yl]-2-cyclopenten-1-yl}carbonyl)-2-nitrobenzenesulfonamide C18H14ClN7O6S 详情 详情
(VI) 55525 tert-butyl 6-chloro-9-[(1R,4S)-4-({[(2-nitrophenyl)sulfonyl]amino}carbonyl)-2-cyclopenten-1-yl]-9H-purin-2-yl(formyl)carbamate C23H22ClN7O8S 详情 详情
(VII) 55526 tert-butyl 6-chloro-9-[(1R,4S)-4-(hydroxymethyl)-2-cyclopenten-1-yl]-9H-purin-2-ylcarbamate C16H20ClN5O3 详情 详情
(VIII) 17650 [(1S,4R)-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopenten-1-yl]methanol C11H12ClN5O 详情 详情
Extended Information